Double Dating on Craigslist, Part 2

Note:  If you have not read yesterday’s installment, Double Dating on Craigslist, Part 1, you should.  Now.  Otherwise, you might not know what the hell is going on.  Head on over there, we’ll wait.  (Just kidding, my wonderful readers.  Wait for them to click out.  Okay, they’re gone.  Let’s begin.)


If this were a TV episode it would begin with the requisite photo montage and a voiceover that says, “Previously on…Sweet Mother.”  So, let’s re-cap.  I was annoyed with lesbo-land and their common “lesbian lazy susan” approach to dating.  As a result, every now and again, I stepped out with one of my straight, lady friends looking for some man-tail.  My dearest friend, Rayanne, had just suffered some heartache.  I did what any good friend would do and put up a crazy, Craigslist advert seeking some potential man-tail to distract her.


And so we almost begin.  I think it’s necessary to give you some backstory, here, before I go into the foibles and hijinks of the actual date.


At the time, Rayanne and I were working a comedy club as comedians that I will call, “The Comedy Barrio” or Barrio for short.  It was one of those interesting ‘ownership’ situations that can only happen in New York.  The Comedy Barrio was above McCann’s pub.  McCann’s pub owned the building and did the majority of its business.  The pub was owned by an Irish ex-pat and was filled with a staff of illegal Irish-Irish folks working as its staff and bartenders.  The bar was amazing, in the way only an Irish pub can be.  The owner at McCann’s had always ‘rented’ the upstairs to a comedy club.  It was originally run by a guy who ended up managing Dane Cook and Jay Mohr.  When their careers got too big, he gave it up.  Enter JC.



JC stepped into the Barrio and took over.  JC was a big, Irish, redheaded, mother of a man.  He’s old school New York and old school Irish-American.  He had a Puerto Rican wife and they have two kids together.  Now, most of the clubs in New York for their weekend talent fight over the huge – nationally known names – for their weekend lineups.  But, not JC, probably because he couldn’t afford them.  So, he went with us, middle level acts, sprinkled with a known name here and there.  The Barrio was a strange place in that we, the middling acts, were grateful for the weekend stage time, however, we had put those named acts up on a pedestal.  Once they started coming in and only doing as well as us middlers, we sort of felt like, “Wait a minute….why are we being paid less and this guy is no where near as good as his resume says…What gives?”  It created a real solidarity among us.  It was sort of like a baseball player getting pulled up from the minors and going, “Hold on a sec, I’m at least as strong as that outfielder.”  We didn’t feel that way about every big act, obviously, but we definitely did about most of them.  It unified us and created a brother/ sisterhood of sorts.


A core group of us middlers played there every single weekend night.  There was JC who acted as the club’s runner, banker, bouncer, booker, and comedian.  There was Niko who ran around with, literally, an ivory tusk in his ear.  He was an enormous black man with a teddy bear heart, plain and simple.  There was Joe who was a dyed in the wool Irish-American from Brooklyn, probably going back several generations, and, as such, he seemed more Italian.  There was Jay a newlywed from the South who lived with his wife in a hipster part of Brooklyn, which he half thumbed his nose at, regularly.  And that was pretty much it.  Those were the main players.  There were lots of ancillary ones, as well, that gave the place color, but mainly these characters set the scene.  Oh, and there was, US – the three, female, comedians, the only ones who JC deemed funny enough to play the room – me, Rayanne, and Miranda.  A black, a Jew, and an Irish woman walk into a…well, you see what I mean, we were almost a living satire – the three of us.  It was fantastic.  You can not re-create the kind of vibe that we had at The Barrio.  Those were magical times.  Magical, magical times.


Back to the Craigslist responses.  Rayanne and I decided on two different sets of boys/ men.  Each pair were cute in a different way and they had also written a little bit about themselves.  We liked the look of them and what they had to say.  Rayanne called them both up.  The one pair didn’t respond for a couple of days and, as a result, Rayanne crossed them off the list.  Now, here’s something important you need to know about Rayanne.


Rayanne is a MASTER dater.  In the days (and with Rayanne usually months) leading up to sex, Rayanne can command a potential boyfriend like a snake charmer controls a python.  It is an incredible sight to behold.  She has them dropping her off and picking her up and paying for flowers and holding doors and sleeping next to her, but not ‘touching’ anything.  I swear, this is the case.  I call this process her “Mormon plan”.  I’m always saying to her, “Oh, are you putting that poor guy through the Mormon plan?”  And she always is.  There’s always some poor soul, WILLINGLY, participating in the Mormon plan.  It’s a strenuous program for these guys, let me tell you.  I don’t know how they survive it.


Rayanne will literally say to them, “Okay, we’re going to have an adult sleepover, but I’m not going to have sex with you yet.  You’re going to sleep here, next to me.  You’re going to be irritated.  You’re going to be thinking about sex all night without getting any.  You’re probably going to get a horrible case of blue balls.  If you’re lucky, I’ll let you touch the breasts, but you’ll have to stop there.  It’s simple.  Are you up for it?  Because if you’re not, we can stop right here.”  Rayanne always did this in such a way that the guys laughed and signed right on for the Mormon plan.  I mean she’s put ever single guy of hers through it and succeeded.  She’s a serial monogamist, so there have been several.


I was more of a ‘kid at the slow camp’ about dating dudes.  My Mormon plan was less stringent and more like a Dollar Menu at McD’s.  You know the dollar menu at McD’s, it’s stuff you’d never try in the ‘awake’ section of your life, but if you have a few drinks, you say feck it – you try this and that and then the next day you try to forget it ever happened at all.  That was my plan.  I’d say, all around, Rayanne’s Mormon regiment was far more successful.


So, pair number 1 had broken the unspoken, Mormon rules by not calling back promptly and they were immediately crossed off the list.  We moved on to duo number 2.  I was totally okay with this because, truth be told, I was way more into pair number 2.  I mean, they were Latino and ADORABLE.  Guy 1 was a brown haired Colombian with glasses who looked like Gael Garcia Bernal and Guy 2 was a blonde haired Spaniard who looked like a young Leonardo DiCaprio.  What could go wrong?


"Si, por favor!"

So cute, it almost seems gay...


Rayanne and I sat in a bar together and had a few drinks to rachet up the courage.  Today, Rayanne would call the Latinos.  She slammed down her drink and said, “Alright, I’m doing it.”  She picked up her phone and dialed.  He answered.  Rayanne was having a lovely conversation with him, so far, but the bar was a bit loud.  So, she stepped outside to finish it.


Rayanne came back in with a big smile on her face.  “It’s set,” she said.  “We’re meeting them at Vino bar around the corner from the Barrio on Saturday night, so we can still do our comedy sets and go on our double date.”


How cool, I thought.  We were going to meet these two hot guys AND get paid to do what we loved – comedy.


Want to know what happened?  Come back tomorrow, where I PROMISE you’ll read the last installment of Double Dating on Craigslist.


Stop it, don’t throw things at me!  I want to get this whole story out, but I don’t want the individual posts to be too long.  In other words, I don’t want to take up too much of your time.  I want to give you doses and I promise tomorrow’s installment will involve SEX and ridiculousness in some way – maybe even all together.  There, now isn’t that worth waiting for?  Maybe even better than d*ck pics.



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You might also like:

Double Dating on Craigslist, Part 1


Photo creds:  leo, gael, pub, feature-double-date